Combining light-harvesting and charge separation in a self-assembled artificial photosynthetic system based on perylenediimide chromophores

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Abstract

Self-assembly of robust perylenediimide chromophores is used to produce an artificial light-harvesting antenna structure that in turn induces self-assembly of a functional special pair that undergoes ultrafast, quantitative charge separation. The structure consists of four 1,7-(3′,5′-di-tert-butylphenoxy)perylene-3,4:9,10-perylene-3,4:9,10-bis(carboximide) (PDI) molecules attached to a single 1,7-bis(pyrrolidin-1-yl)perylene-3,4:9,10-perylene-3,4:9,10-bis(carboximide) (5PDI) core, which self-assembles to form (5PDI-PDI4)2 in toluene. The system is characterized using both structural methods (NMR, SAXS, mass spectroscopy, and GPC) and photophysical methods (UV-vis, time-resolved fluorescence, and femtosecond transient absorption spectroscopy). Energy transfer from (PDI)2 to (5PDI)2 occurs with τ = 21 ps, followed by excited-state symmetry breaking of 1*(5PDI)2 to produce 5PDI•+-5PDI•- quantitatively with τ = 7 ps. The ion pair recombines with τ = 420 ps. Electron transfer occurs only in the dimeric system and does not occur in the disassembled monomer, thus mimicking both antenna and special pair function in photosynthesis.

Original languageEnglish
Pages (from-to)12268-12269
Number of pages2
JournalJournal of the American Chemical Society
Volume126
Issue number39
DOIs
Publication statusPublished - Oct 6 2004

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Perylene
Chromophores
Self assembly
Antennas
Light
Photosynthesis
Crystal symmetry
Absorption spectroscopy
Excited states
Energy transfer
Toluene
Monomers
Fluorescence
Nuclear magnetic resonance
Spectroscopy
Molecules
Electrons
Energy Transfer
Ions
Mass Spectrometry

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

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title = "Combining light-harvesting and charge separation in a self-assembled artificial photosynthetic system based on perylenediimide chromophores",
abstract = "Self-assembly of robust perylenediimide chromophores is used to produce an artificial light-harvesting antenna structure that in turn induces self-assembly of a functional special pair that undergoes ultrafast, quantitative charge separation. The structure consists of four 1,7-(3′,5′-di-tert-butylphenoxy)perylene-3,4:9,10-perylene-3,4:9,10-bis(carboximide) (PDI) molecules attached to a single 1,7-bis(pyrrolidin-1-yl)perylene-3,4:9,10-perylene-3,4:9,10-bis(carboximide) (5PDI) core, which self-assembles to form (5PDI-PDI4)2 in toluene. The system is characterized using both structural methods (NMR, SAXS, mass spectroscopy, and GPC) and photophysical methods (UV-vis, time-resolved fluorescence, and femtosecond transient absorption spectroscopy). Energy transfer from (PDI)2 to (5PDI)2 occurs with τ = 21 ps, followed by excited-state symmetry breaking of 1*(5PDI)2 to produce 5PDI•+-5PDI•- quantitatively with τ = 7 ps. The ion pair recombines with τ = 420 ps. Electron transfer occurs only in the dimeric system and does not occur in the disassembled monomer, thus mimicking both antenna and special pair function in photosynthesis.",
author = "Boris Rybtchinski and Sinks, {Louise E.} and Wasielewski, {Michael R}",
year = "2004",
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